GB989144A - Polyether polyols and polyurethane foams derived therefrom - Google Patents

Polyether polyols and polyurethane foams derived therefrom

Info

Publication number
GB989144A
GB989144A GB2781963A GB2781963A GB989144A GB 989144 A GB989144 A GB 989144A GB 2781963 A GB2781963 A GB 2781963A GB 2781963 A GB2781963 A GB 2781963A GB 989144 A GB989144 A GB 989144A
Authority
GB
United Kingdom
Prior art keywords
diisocyanate
specified
glycol
anhydrohexitols
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2781963A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of GB989144A publication Critical patent/GB989144A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/487Polyethers containing cyclic groups
    • C08G18/4883Polyethers containing cyclic groups containing cyclic groups having at least one oxygen atom in the ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

The invention comprises polyoxypropylene anhydrohexitols of hydroxyl number 350-750 containing no more than 10 mol. per cent polyoxypropylene glycol. The compounds may be prepared by reacting propylene oxide with an anhydrohexitol at 90-150 DEG C. in the absence of water and in the presence of a basic catalyst. Sufficient propylene oxide may be added to form chains 2-10 units long on some or all of the hydroxyl groups. Anhydrohexitols specified are 1,4-, 1,5-, 2,6-, and 3,5- anhydrosorbitol and anhydromannitol and 1,4: 3,6-dianhydrosorbitol or mixtures thereof. They may be obtained by reducing the corresponding hexose. 0.01-0.5 molecules of catalyst may be used per hydroxy group. Catalysts specified are the hydroxides, methoxides and ethoxides of sodium and potassium and the alkali metal alcoholates of the anhydrohexitols. The reaction may be carried out under a nitrogen atmosphere and at elevated pressure. A solvent may be employed, e.g. dimethyl formamide, dimethyl sulphoxide, a hydrocarbon, ether or heterocyclic base. A basic solvent may also function as a catalyst. In examples (3-6) the product is purified by dilution with water and passage down a cation-exchange resin column.ALSO:A polyurethane foam may be produced by adding a polyisocyanate and a blowing agent to a polyol of OH number 350-750 prepared by interacting an anhydro-hexitol and propylene oxide at 90-150 DEG C., in the presence of a basic catalyst and in the absence of water. Anhydrohexitols specified are 1,4-, 1,5-, 2,5- and 3,6- anhydrosorbitol, 1,4-, 1,5-, 2,6- and 3,6- anhydromannitol, 1,4,3,6 - di - anhydrosorbitol and dianyhydromannitol. Mixtures of isomers may be used. Catalysts specified are the hydroxides, methoxides and ethoxides of sodium and potassium and the alkali metal alcoholates of the anhydrohexitols. 0.01-0.5 equivalents may be used per equivalent of hydroxyl group. The propylene oxide addition reaction may be carried out at atmospheric or an elevated pressure of an inert gas, e.g. N2 and a solvent may optionally be used. Solvents specified are: n-hexane, ligroin, benzene, xylene, dioxane, diethylene glycol, diethyl ether, dimethyl formamide, dimethyl sulphoxide, N - acylmorpholines, N - methylpyrrolidone, N - ethyl - pyrrolidone, pyridine, picoline and tri-n-butylamine. The addition product may have 2-10 oxypropylene units per molecule and may contain up to 10% of polyoxypropylene glycol in admixture. In polyurethane production the polyols of the invention may be mixed with other polyols, e.g. linear polyethers, polyesters, aromatic polyethers, and sorbitol centred polyethers. Isocyanates specified are: ethylene diisocyanate, ethylidene diisocyanate, propylene-1,2 - diisocyanate, butylene - 1,2 - diisocyanate, hexylene - 1,6 - diisocyanate, cyclohexylene - 1, 2 - diisocyanate, m - phenylene diisocyanate, tolylene - 2,4 - diisocyanate, tolylene - 2,6 - diisocyanate, 3,31 - dimethyldiphenyl - 4, 41 - diisocyanate, 3,31 - dichlorodiphenyl - 4, 41 - diisocyanate, triphenylmethane - 4, 41,411 - triisocyanate, naphthalene-1, 4-diisocyanate reaction products of these with: hexane-1,2,6-triol, 1,1,1-trimethylolpropane, glycerol, propylene glycol, dipropylene glycol, tripropylene glycol, or mono-, di- or tri-ethylene glycol. Blowing agents specified are H2O, CCl2, F2, CCl3F and azo compounds The reaction may be a continuous process, a one-shot process or a prepolymer two-stage reaction. Other additives may be catalysts, e.g. N-methyl morpholine, triethylamine, N,N, N1, N1-tetra(2-hydroxypropyl) ethylene diamine, dibutyltin dilaurate, dibutyltin di(2-ethylhexoate), stannous octoate and stannous 2-ethylhexoate, foam stabilizers, e.g. polydimethylsiloxane, alkylsilane-polyoxyalkylene block copolymers, sorbitan monostearate and glycerol monooleate, pigments, fillers, e.g. glass fibre, nylon fibre, wool, polyvinyl chloride, mica, silica gel, alumina gel, asbestos and zinc oxide, antioxidants and stabilizers. The products may be rigid and of uniform cell size.
GB2781963A 1962-07-17 1963-07-12 Polyether polyols and polyurethane foams derived therefrom Expired GB989144A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP3049462 1962-07-17
JP3473262 1962-08-11

Publications (1)

Publication Number Publication Date
GB989144A true GB989144A (en) 1965-04-14

Family

ID=26368856

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2781963A Expired GB989144A (en) 1962-07-17 1963-07-12 Polyether polyols and polyurethane foams derived therefrom

Country Status (2)

Country Link
DE (1) DE1545001A1 (en)
GB (1) GB989144A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110799561A (en) * 2017-06-22 2020-02-14 株式会社三养社 Composition for forming environmentally friendly polyurethane foam and method for producing polyurethane foam
CN114222770A (en) * 2019-07-12 2022-03-22 株式会社三养社 Anhydrosugar alcohol-alkylene glycol composition, anhydrosugar alcohol-based urethane-modified polyol composition, and use thereof for epoxy resin composition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008011683A1 (en) * 2008-02-28 2009-09-03 Bayer Materialscience Ag Process for the preparation of polyols

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110799561A (en) * 2017-06-22 2020-02-14 株式会社三养社 Composition for forming environmentally friendly polyurethane foam and method for producing polyurethane foam
EP3643732A4 (en) * 2017-06-22 2021-03-24 Samyang Corporation Composition for forming environmentally friendly polyurethane foam and method for manufacturing polyurethane foam
CN110799561B (en) * 2017-06-22 2022-02-11 株式会社三养社 Composition for forming environmentally friendly polyurethane foam and method for producing polyurethane foam
EP3981815A1 (en) * 2017-06-22 2022-04-13 Samyang Corporation Composition for forming environmentally friendly polyurethane foam and method for manufacturing polyurethane foam
EP4321550A3 (en) * 2017-06-22 2024-05-15 Samyang Corporation Composition for forming environmentally friendly polyurethane foam and method for manufacturing polyurethane foam
CN114222770A (en) * 2019-07-12 2022-03-22 株式会社三养社 Anhydrosugar alcohol-alkylene glycol composition, anhydrosugar alcohol-based urethane-modified polyol composition, and use thereof for epoxy resin composition
EP3998299A4 (en) * 2019-07-12 2023-07-26 Samyang Corporation Anhydrous alcohol-alkylene glycol composition, anhydrous alcohol-based urethane-modified polyol composition, and uses of same for expoxy resin composition
CN114222770B (en) * 2019-07-12 2024-04-05 株式会社三养社 Anhydrosugar alcohol-alkylene glycol composition, anhydrosugar alcohol-based urethane-modified polyol composition, and uses thereof

Also Published As

Publication number Publication date
DE1545001A1 (en) 1969-07-24

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